p-Fluoronitrobenzene → HCID 44609574, compound

Participants

Reaction Steps

Under ice-cooling, 2-aminocarbonylamino-6-hydroxyindole-3-carboxamide (Compound No.2-1, 1.3 g, 5.5 mmol) in anhydrous N,N-dimethylformamide (7 mL) was added dropwise to a suspension of 60% sodium hydride (450 mg, 11 mmol) in anhydrous N,N-dimethylformamide (15 mL) over a period of 5 minutes and the mixture was stirred for 5 minutes. Moreover 4-fluoronitrobenzene (640 μL, 6.0 mmol) was added thereto, and the mixture was stirred for 15 minutes at room temperature and stirred overnight at 60° C. After cooling, the reaction solution was diluted with water (300 mL) and extracted with ethyl acetate (200 mL). The organic layer was washed with saturated aqueous sodium hydrogen carbonate (200 mL) and brine (200 mL), and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained solid was filtered off and washed with a mixed solvent of chloroform-diethyl ether solution (1:2, 60 mL). The solid was dried at 40° C. for 1 hour under reduced pressure to give the title compound (1.2 g) as a brown solid (59%).

Provenance & Evidence